NP-MRD: Showing NP-Card for methylephedrine (NP0290524)

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Record Information

Version

2.0

Created at

2022-09-09 21:15:10 UTC

Updated at

2022-09-09 21:15:10 UTC

NP-MRD ID

NP0290524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methylephedrine

Description

Methylephedrine belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Methylephedrine is a very strong basic compound (based on its pKa). methylephedrine is found in Ephedra sinica. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -1.6910   -1.5788   -0.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -0.1018   -0.8443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1189    0.3260   -1.3530 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1280   -0.2869   -2.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081   -0.0024   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    0.9732    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6468    0.7397    1.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135   -0.5671    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -1.5669    0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4996   -1.2813   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907    0.4801    0.3659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003    0.1667    1.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1478    1.8810    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345   -1.9065   -1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7709   -1.8079   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4101   -2.1818   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1920    0.3397   -1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.4206   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118   -0.4323   -2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969    1.9780    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149    1.5070    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -0.7838    1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -2.5579    0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669   -2.0809   -0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7255    1.1090    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205   -0.0189    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4297   -0.6035    1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654    2.2713   -0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    2.5112    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    2.0552    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 11 13  1  0
 10  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  6
  3 18  1  6
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6   10                                                       
CONECT    9    1   11   12                                                  
CONECT   10    7    8   11                                                  
CONECT   11    9   10   13                                                  
CONECT   12    2    3    9                                                  
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S)-(-)-N-Methylephedrine	HMDB
(1Rs,2Rs)-2-Dimethylamino-1-phenylpropan-1-ol	HMDB
DL-Methylephedrine hydrochloride	HMDB
Erythro-alpha-[1-(dimethylamino)ethyl]benzyl alcohol	HMDB
L-Methylephedrine hydrochloride	HMDB
Methylephedrin	HMDB
N,N-Dimethylnorephedrine	HMDB
N,N-Dimethylnorephedrine2-dimethylamino-1-phenylpropanol	HMDB
N-Methylephedrine	HMDB
N-Methylephedrine hydrochloride, (r,s)-(+-)-isomer	HMDB
N-Methylephedrine hydrochloride, (S-(r,r))-isomer	HMDB
N-Methylephedrine hydrochloride, (r,r)-(+-)-isomer	HMDB
N-Methylephedrine hydrochloride, (r,s)-isomer	HMDB
N-Methylephedrine, (r,s)-(+-)-isomer	HMDB
N-Methylephedrine, (r,s)-isomer	HMDB
Methylpseudoephedrine	HMDB
N-Methylephedrine, (R-(r,s))-isomer	HMDB
N-Methylephedrine hydrochloride, (R-(r,s))-isomer	HMDB
N-Methylephedrine, (r,r)-isomer	HMDB
N-Methylephedrine, (S-(r,r))-isomer	HMDB
Methylephedrine	MeSH

Chemical Formula

C₁₁H₁₇NO

Average Mass

179.2588 Da

Monoisotopic Mass

179.13101 Da

IUPAC Name

2-(dimethylamino)-1-phenylpropan-1-ol

Traditional Name

N-methylephedrine

CAS Registry Number

Not Available

SMILES

CC(C(O)C1=CC=CC=C1)N(C)C

InChI Identifier

InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3

InChI Key

FMCGSUUBYTWNDP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ephedra sinica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.73	ALOGPS
logP	1.7	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.98 m³·mol⁻¹	ChemAxon
Polarizability	20.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041932

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4221

KEGG Compound ID

C13639

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylephedrine

METLIN ID

Not Available

PubChem Compound

4374

PDB ID

Not Available

ChEBI ID

90046

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methylephedrine (NP0290524)

MOL for NP0290524 (methylephedrine)

3D MOL for NP0290524 (methylephedrine)

3D SDF for NP0290524 (methylephedrine)

3D-SDF for NP0290524 (methylephedrine)

PDB for NP0290524 (methylephedrine)

3D PDB for NP0290524 (methylephedrine)

SMILES for NP0290524 (methylephedrine)

INCHI for NP0290524 (methylephedrine)

Structure for NP0290524 (methylephedrine)

3D Structure for NP0290524 (methylephedrine)